The Sex Machine

Jon Gross is having more sex than you. Way, waaaaay more sex, and with way more people’s spouses. So how exactly did this middle-aged New England plumbing-supplies salesman find the secret to free love, make friends with porn stars and multimillionaires, and become America’s king of swingers?

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A couple enjoys some time on a clothing-optional catamaran sunset “booze cruise” in Jamaica. / Photograph by Brian Finke

“She’s stunning,” I said. What else can you say when your seatmate on a flight from Tampa to Boston angles his cell phone to show you a selfie of a naked woman? Blond, in her mid-twenties, tan, and toned, she was in the shower aiming the camera down from above. I noticed a constellation of little tattoos near her breast. The woman, he said, was his girlfriend.

Turns out my seatmate, Jon Gross, was the sharing type. Even on the tarmac, before we’d taken off, he was letting me read his text messages to this woman. In one text, laced with exclamation points, the girlfriend announced she’d met a special someone. Gross, deploying many exclamation points of his own, congratulated her and wished her the best.

As I read the messages, my head was spinning. Why was his girlfriend telling him about a new man? Why wasn’t he bothered? And how had he landed this girl in the first place? Gross wasn’t a bad-looking guy. He had a well-proportioned face, hazel eyes, and a charming, impish smile. But he was, by his own admission, 57, mostly bald, 5-foot-4, and 210 pounds. Plus, he was dressed like a slob in an oversize cotton T-shirt and athletic shorts.

As we talked more, my confusion only deepened. He mentioned other girls and showed me pictures of them: a thirtysomething blond woman in lingerie, who made her living as a marketing executive; a brunette DJ who could easily have passed for a model. Then he mentioned his wife, a petite woman closer to his age. “My wife’s a beautiful woman,” he said, gazing at a picture of her before flipping to another photo, which left me even more baffled: his wife and the blond marketing executive on a beach, arms around each other, smiling.

During the next two hours, Gross sketched out his life story. A Sharon native, he’d been a computer and radio geek as a kid, a plumbing-equipment salesman through early middle age, and, later, one of New England’s Internet pioneers. These days, though, he makes his living as the head of a company called Jon’s Fluffernutters, which throws round-the-clock parties for hundreds of naked, free-loving adult members, most of whom participate in secret.

When I met Gross last spring, he was recovering from one of these blowouts: a three-night-long fete he’d hosted at a “clothing optional” resort called Caliente. The event had been a cross-promotion, he told me, with his other business—the somewhat infamous Jamaican nudist resort Hedonism II, which he co-owns. His business partner, and the money behind the operation, is Harry Lange, former head of Boston’s $17 billion Fidelity Magellan Fund. A longtime Fluffernutters member, Lange had partied with Gross for years—the two had sipped margaritas naked in Jamaica and cavorted with Playboy Bunnies at Hugh Hefner’s mansion in L.A.—before buying the resort with him in 2013. More surprising than anything, though, was that Gross ran his hospitality empire not from Miami or Las Vegas, but from an office building near his home in Manchester, New Hampshire.

At first, it was tough to believe anything Gross told me, but the quick stream of pictures, videos, and messages he showed as evidence were hard to dismiss. In addition to his girlfriends’ selfies, Gross showed me several glamour shots, including one in which he was standing at a red-carpet event with his arm around a grinning Ariana Grande. Gross also showed me his text messages with world-famous porn star Ron Jeremy. In a recent message, Jeremy was texting Gross about where to find an after-party.

Yet Gross didn’t strike me as a namedropper. In fact, he seemed more interested in talking about his ordinary customers. He told me his target demographic is married, middle-class couples who sneak away from their families and friends on vacations to get naked and sleep with one another. Gross and his wife, he explained, weren’t just instigators but active participants. They’re in an open marriage themselves: They are both free to sleep with whomever they like, no strings attached, and like to spend their vacations at Hedonism II partying naked with clients.

After my chance encounter with Gross, I got to know many of these people—teachers, accountants, police officers, and lawyers from throughout New England and around the world. There are thousands of them, all happy to pay for the privilege of partying with Jon Gross. The ones I met spoke of him in fawning terms, as if he were the beloved pastor of a megachurch. Except instead of salvation, Gross’s flock seeks liberation through nudity, hard partying, and free love, one blowout weekend at a time. “What’s better than making a living throwing a party, and being the man, and helping people’s lives, and people actually loving you for it?” Gross says. “That’s pretty unbelievable, you know.”